Jail Time? 6 Hollywood Actors With the Most Arrests

It seems like it happens all the time. A famous actor or actress becomes infamous, not because of their latest movie or some new development in their love life, but because they’re behind bars. Over the years, dozens of Hollywood’s biggest names have been arrested — and for a wide variety of reasons. Some celebrity arrests, like Hugh Grant or Shia LeBeouf’s, are a cause for lighthearted ridicule. Others, like OJ Simpson‘s, become a national obsession.

Celebrity arrests aren’t always just a headline, though. Some celebrities’ legal troubles point to serious issues in their personal lives. And sometimes, their encounters with the law shine a light on issues like drug abuse, alcoholism, and domestic abuse.

Many celebrities who get arrested eventually straighten up their act. But a few have had a surprising number of run-ins with law enforcement. Here are six famous Hollywood actors that have been arrested a surprising number of times.

1. Martin Sheen

Martin Sheen as President Josiah Bartlett in a scene from NBC's 'The West Wing'

Martin Sheen in The West Wing | Source: NBC

There’s one thing that’s very clear about Martin Sheen: Politics is in his blood. Over the years, he’s starred in films like Francis Ford Coppola’s Vietnam epic Apocalypse Now and as a White House adviser in The American President. Most of us know him as the beloved President Bartlet in NBC’s hit series, The West Wing. But his other endeavors also have a strong political slant — he’s a passionate activist who once said that while he makes his living as an actor, his off-screen work is what “keeps him alive.” It’s also kept him in frequent contact with police. Since the mid-1980s, Sheen has been arrested 66 times for civil disobedience. And he hasn’t let his record keep him from demonstrating and speaking out about the causes he feels passionate about: anti-war activism, nuclear proliferation, workers’ rights, and environmental conservation — just to name a few.

2. Robert Downey Jr.

Robert Downey Jr. plays Tony Stark in a scene from the movie 'Iron Man'

Robert Downey Jr. in Iron Man | Source: Marvel Studios

He currently plays one of the most charismatic and brilliant superheroes ever created. But for years, Robert Downey Jr. was at an all-time low as he struggled with addiction and had numerous run-ins with the law as a result. Over the course of several years in the late ’90s and early 2000s, the Iron Man star was arrested six times for drug-related charges. His addiction problems — and subsequent legal troubles, led to him being fired from numerous projects, including his “comeback” turn on Ally McBeal. He spent time in jail and in rehab centers before finally turning a corner. He’s avoided any further legal trouble — and even received a gubernatorial pardon in 2015 — and reestablished himself as one of Hollywood’s most popular actors.

3. Lindsay Lohan

Lindsay Lohan as Cady in a scene from 'Mean Girls'

Mean Girls | Source: M.G. Films

For a brief moment in time, Lindsay Lohan was truly America’s sweetheart. But the high pressure of fame got to the young starlet, and she found herself struggling with alcohol and drug addictions. Since 2007, she’s been arrested at least four times and had her probation revoked another four times for charges stemming from drug and alcohol use and shoplifting. The 29-year-old suffered financial and professional troubles on top of her legal issues, and seemingly spent years going from rehab to jail and back again. In 2015, Lohan successfully completed her probation and has maintained a low profile since.

4. Michelle Rodriguez

Michelle Rodriguez in a scene from 'Fast & Furious 6'

Fast & Furious 6 | Source: Relativity Media

She’s starred in blockbuster franchises and wildly popular television series. But Michelle Rodriguez has also made headlines for her non-acting activities. The Fast & Furious and LOST star has been arrested five times, for charges ranging from assault to driving under the influence. She also spent nearly three weeks in jail after violating her probation in 2008.

5. Rip Torn

Rip Torn as Patches O'Houlihan in a scene from 'Dodgeball'

DodgeBall: A True Underdog Story | Source: Fox 2000 Pictures

Rip Torn has won awards and countless fans for his perfect comedic timing. But the 78-year-old The Larry Sanders Show and Dodgeball star also has a troubled personal life. He’s been arrested at least four times — for drunk driving and, most recently, for breaking into a bank while intoxicated. According to reports, Torn believed that he was entering his own home; regardless, he was charged with a long list of offenses, including carrying a firearm illegally, burglary, and criminal mischief.

6. Charlie Sheen

Charlie Sheen in a scene from CBS's sitcom 'Two and a Half Men'

Two and a Half Men | Source: CBS

Charlie Sheen, like his father, has had plenty of encounters with law enforcement. Unfortunately, his had less to do with political activism and more to do with his own personal demons. Sheen has been a staple in celebrity tabloids for his notorious partying — but he’s also been arrested twice for acts of violence against women, and a third time for violating probation. His erratic behavior has unfortunately made him more famous than his once-promising career ever did.

Follow Katherine Webb on Twitter @katiedoubleyew.

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